- Preparation method of iprodione
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The invention discloses a preparation method of iprodione, which comprises of mixing N-[[(3,5 dichlorophenyl) amino] carbonyl] glycine with an organic solvent to react by the action of a catalyst A to generate 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione, and allowing 3-(3,5-dichlorophenyl)-2,4-imidazolidinedione to react with isopropyl isocyanate by the action of a catalyst B and a catalyst C to generate iprodione, wherein the catalyst A is a mixture of concentrated sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid; the catalyst B is a mixture of ammonium carbonate, sodium bicarbonate and sodium carbonate; and the catalyst C is a mixture of pyridine and triethylamine. A content of the finished product, namely iprodione prepared by the method reaches above 97%, and the preparation cost of iprodione is greatly lowered.
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Paragraph 0039-0046; 0050-0057
(2017/10/28)
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- Broadcast carriers for pesticides and their use
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This invention relates to certain natural diatomaceous earth granule compositions which can be broadcast, i. e., dry spread on the soil to deliver a pesticide or fertilizer. The granules retain their physical integrity when spread, and have the unique property to spontaneously disintegrate when irrigation water is applied or rainfall hits the particle. Upon wetting, the particle disintegrates (blooms) to cover the soil surface. This bloom can cover an area many times the original area covered by the granule. The granules have high loadings of the diatomaceous earth, i.e. from about 35 to about 95 weight percent and contain from about 5 to about 40 weight percent of a surfactant system which exhibits excellent disintegration; rewetting and binding properties. Bioactive compounds can be loaded at up to 60 weight percent of the granule. Bioactive compounds may be formulated products or technical grades and may be homogeneously distributed throughout the granule or spray impregnated onto the granule.
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- Pyrimidine derivatives, process and intermediate products for their preparation and pesticides or fungicides containing these derivatives
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Pyrimidine compounds I wherein X is C(CO2CH3)═NOCH3, C(CONHCH3)═NOCH3, C(CO2CH3)═CHOCH3, C(CO2CH3)═CHCH3or N(CO2CH3)—OCH3; R1, R2are hydrogen, alkyl, haloalkyl or alkoxy; A is R3is hydrogen, alkyl, haloalkyl, phenoxyalkyl, cycloalkyl, cyano, alkoxy, hydroxyl or halogen; R4is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, cycloalkyl or alkoxy; Y is hydrogen, hydroxyl, halogen, optionally substituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio, or their salt, their synthesis and intermediates therefore, and their activity against fungi or animal pests.
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- Fungicidal composition for seed dressing
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The present invention relates to a fungicidal composition intended for the protection of the multiplication products of cultivated plants, containing: (a) 2-(4-chlorobenzylidene)-5,5-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-1-cyclopentanol; (b) one or more fungicides suitable for the protection of the said multiplication products, optionally one or more insecticides, (c), an agriculturally acceptable inert vehicle and an agriculturally acceptable surfactant. The invention also relates to a method for protecting the multiplication products of plants against fungal diseases using these compositions.
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- Plant-protective pesticidal composition
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The invention relates to a plant-protective solution containing 2.5 to 40 % by weight of one or more water-insoluble plant-protective ingredient(s) 20 to 71.5 % by weight of dimethylformamide and/or dimethylsulfoxide and/or acetone as water-miscible solvent, 10 to 71.5 % by weight of furfurol and/or furfuryl alcohol as partially water-miscible solvent, 1 to 15 % by weight of commonly used additives such as anionic and/or nonionic surface active agents and macromolecules. The invention also relates to the ready-for-use plant-protective suspension containing 0.2 to 10 % by weight of one or more water-insoluble plant-protective ingredient(s) with a particle size of 0.1 to 50 μm, 0 to 60 % by weight of a fertilizer, 0.2 to 10 % by weight of dimethylformamide and/or dimethylsulfoxide and/or acetone as water-miscible solvent, 0.2 to 10 % by weight of furfurol and/or furfuryl alcohol as partially water-miscible solvent, 0.05 to 2.5 by weight of a commonly used additive such as anionic and/or nonionic surface active agents macromolecules and water in an amount supplementing up to 100 % by weight.
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- Kinetics and Mechanisms of Cyclization in Acidic Media of N-N-glycine to Hydantoins: Iprodione and Its Isomer
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N--N-glycine (1) cyclizes quantitatively and irreversibly at 50 deg C in the pH range 0.5-6 by two parallel paths to give iprodione (2) and its isomer 3.Formation of the antifungal agent 2 is characterized by a general base catalysis with carboxylate anions, water, and hydroxide ion (β = 0.38) and a solvent isotope effect of 2.90.These results are consistent with a specific base catalyzed addition of the enolate anion of the ureido group to the carboxylic function of hydantoic acid (pKa1 = 4.25) to givetetrahedral intermediate T- whose general acid catalyzed decomposition is rate limiting.Formation of isomer 3 occurs by a specific base catalyzed cyclization of 1 compatible with a nucleophilic attack of the enolate anion of the ureido moiety on the carboxylic group in the pH range 2-6.Below pH 2 hydantoic acid undergoes a specific acid catalysed and spontaneous hydrolysis involving a nucleophilic attack of the ureido enol on the carboxylic function, protonated or not, respectively.Formation of iprodione is general base catalysed while that of its isomer is not: this can be explained by the change in basicity of the leaving groups from the tetrahedral intermediate, i.e., the N- (pKa2 = 11.7) and the N-isopropylureido (pKa3 ca. 18) anions, respectively.
- Belafdal, Omar,Bergon, Michel,Calmon, Michelle,Calmon, Jean Pierre
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p. 4193 - 4198
(2007/10/02)
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- Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins
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1. Process for the manufacture of N-substituted 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins of the formula: STR1 in which R1 =alkyl (C1 -C4) or phenyl and R2 =H or alkyl (C1 -C4). 2. This process comprises two steps: a. reacting phosgene with 3-(3,5-dichlorophenyl)-hydantoin in an inert organic solvent medium, in the presence of an acid acceptor, in order to form 1-chlorocarbonyl-3-(3,5-dichlorophenyl)-hydantoin, and b. reacting the chlorocarbonyl formed with an amine HNR1 R2 in an inert organic solvent, in the presence of an acid acceptor. 3. This process makes it possible to obtain the products I, which can be used as agricultural fungicides, with good yields.
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- Process for the preparation of 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins
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Fungicidal 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins are prepared by reacting 3 mols an isocyanate of the general formula R -- N = C = 0 (wherein R is alkyl of 1-4 carbons or alkenyl of 2-4 carbons) with one mol of 3-(3,5-dichlorophenyl)-ureidoacetic acid in an anhydrous medium in the presence of an organic base.
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